(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol

Base Information

• Chemical Name: (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol
• CAS No.: 112068-01-6
• Molecular Formula: C₁₇H₁₉NO
• Molecular Weight: 253.344
• Hs Code.: 29339900
• UNII: K3HE3KC32M
• DSSTox Substance ID: DTXSID50369275
• Nikkaji Number: J370.862D
• Wikidata: Q72473246
• Mol file: 112068-01-6.mol

Synonyms:112068-01-6;(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol;(S)-Diphenyl(pyrrolidin-2-yl)methanol;alpha,alpha-Diphenyl-L-prolinol;(S)-(-)-2-(Diphenylhydroxymethyl)pyrrolidine;diphenyl-[(2S)-pyrrolidin-2-yl]methanol;(S)-1,1-Diphenylprolinol;(S)-(-)-Diphenylpyrrolidinemethanol;K3HE3KC32M;(S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol;(S)-alpha,alpha-Diphenylprolinol;UNII-K3HE3KC32M;(-)-alpha,alpha-Diphenylprolinol;(s)-alpha,alpha-diphenylpyrrolidinemethanol;MFCD00075506;(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol;(2S)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol;2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-;2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (2S)-;S-(-)-1,1-Diphenylprolinol;Diphenyl(2-pyrrolidinyl)methanol #;(R)-(+)-alpha,alpha-Diphenylprolinol;(S)-(-)-alpha,alpha-Diphenylprolinol;(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine;S-(-)-Diphenylprolinol;A,A-Diphenyl-L-prolinol;SCHEMBL239738;(S)-Diphenylpyrrolidinemethanol;DTXSID50369275;CS-D1383;FD1262;(R)-(+) alpha,alpha-diphenylprolinol;AKOS005144224;AKOS005259761;AC-6129;AC-6131;CS-O-15225;diphenyl[(2S)-pyrrolidin-2-yl]methanol;AS-12468;BP-11493;.ALPHA.,.ALPHA.-DIPHENYL-L-PROLINOL;AM20020205;D2735;S)-(-)-A,A-Diphenyl-2-pyrrolidinemethanol;(-)-.ALPHA.,.ALPHA.-DIPHENYLPROLINOL;(S)-.ALPHA.,.ALPHA.-DIPHENYLPROLINOL;(S)-alpha,alpha-diphenyl-2-pyrrolidine methanol;Q-102732;(S)-(-)- alpha , alpha -Diphenyl-2-pyrrolidinemethanol;(S)-.ALPHA.,.ALPHA.-DIPHENYLPYRROLIDINEMETHANOL;(-)-.ALPHA.,.ALPHA.-DIPHENYL-2-PYRROLIDINEMETHANOL;(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol, 99%;(2S)-.ALPHA.,.ALPHA.-DIPHENYL-2-PYRROLIDINEMETHANOL;2-PYRROLIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, (2S)-;2-PYRROLIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, (S)-

Chemical Property of (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol

Chemical Property:

• Appearance/Colour: white to beige crystals or crystalline powder
• Vapor Pressure: 1.67E-07mmHg at 25°C
• Melting Point: 77-80 ºC
• Refractive Index: -66.5 ° (C=3, CHCl3)
• Boiling Point: 411.3 ºC at 760 mmHg
• PKA: 13.15±0.29(Predicted)
• Flash Point: 133.3 ºC
• PSA: 32.26000
• Density: 1.128 g/cm³
• LogP: 3.00330
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in chloroform.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 253.146664230
• Heavy Atom Count: 19
• Complexity: 261

Purity/Quality:

98.0%min, ee: 99.0%min ^*data from raw suppliers

(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O
• Isomeric SMILES: C1C[C@H](NC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O
• Uses: suzuki reaction (S)-(-)-alpha,alpha-Diphenylprolinol is used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones. Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.

Technology Process of (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol

There total 53 articles about (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(S)-diphenylprolinol sulfate → (S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 - 25 ℃; for 0.5h;

DOI:10.15227/orgsyn.074.0050

Reference yield: 99.0%

7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one (160424-29-3) → (S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6)

Guidance literature:

With potassium hydroxide; In methanol; for 4h; Heating;

Reference yield: 96.0%

(S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) + phenylmagnesium bromide (100-58-3) → (S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6)

Guidance literature:

(S)-proline-N-ethyl carbamate methyl ester; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

With potassium hydroxide; In methanol; for 16h; Reflux; Inert atmosphere;

DOI:10.3390/molecules17055626

upstream raw materials:

ethyl (2S)-pyrrolidine-2-carboxylate

diphenyl(pyrrolidin-2-yl)methanol

N-(benzyloxycarbonyl)-(S)-proline methyl ester

(S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine

Downstream raw materials:

(S)-N-(2-carbomethoxybenzoyl)-2-(diphenylhydroxymethyl)pyrrolidine

(S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine

(S)-diphenyl(1-methylpyrrolidin-2-yl)methanol

7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one

Refernces

• 1、 Eschmann, Christian,Song, Lijuan,Schreiner, Peter R.. "London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction". supporting information. p. 4823 - 4832. Retrieved 2021/02/01.
• 2、 Gao, En,Li, Meng,Duan, Lili,Li, Lin,Li, Yue-Ming. "Isosteric expansion of the structural diversity of chiral ligands: Design and application of proline-based N,N′-dioxide ligands for copper-catalyzed enantioselective Henry reactions". . . Retrieved 2019/08/16.